A waterfall cascading into a turquoise pool surrounded by lush greenery.

Middlesex County Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Middlesex County vacation rentals

A modern kitchen with a built-in oven, a refrigerator, and a dining area with a table set for four.

1. Phoenix Park Villas Portmore

Phoenix Park Villas Portmore
4.0 star property
Portmore
9.8 out of 10, Exceptional, (6 reviews)
"I will definitely recommend that you stay here is so peaceful security are strictly on point with everything and the comfort of the home is great will be staying back for sure ."
United States
Kimoya
The price is P14,081
P24,615 total
includes taxes & fees
Oct 2 - Oct 3
Phoenix Park Villas Portmore
A modern living room with a white sofa, a glass coffee table, and a staircase leading to an upper level.

2. Tuscany Sun Villa at Legacy Townhouse

Tuscany Sun Villa at Legacy Townhouse
2.0 star property
Thompson Town
The price is P46,992
P54,103 total
includes taxes & fees
Oct 14 - Oct 15
Tuscany Sun Villa at Legacy Townhouse
A balcony with a view of a pool and a building in the background.

3. Caldo Tours

Caldo Tours
2.5 star property
Ewarton
10.0 out of 10, Exceptional, (3 reviews)
"Very inviting and the owner's are wonderful people that keeps you comfortable and satisfied "
United States
Stephen
The price is P7,322
P8,117 total
includes taxes & fees
Oct 6 - Oct 7
Caldo Tours
A living room with a sofa, a coffee table, and a TV mounted on the wall. There is a kitchen area in the background with a window and a bar stool.

4. Wave Crest Resort Race Course

Wave Crest Resort Race Course
2.5 star property
Oracabessa
The price is P6,618
P7,673 total
includes taxes & fees
Oct 2 - Oct 3
Wave Crest Resort Race Course
A large swimming pool with a clear view of the ocean in the background, surrounded by resort-style buildings.

5. The Crest - Serenity Oasis Villa

The Crest - Serenity Oasis Villa
2.0 star property
St. Ann's Bay
8.0 out of 10, Very good, (1 review)
"Location is beautiful and very secure and safe. The house and pool were lovely as well. "
United States
Laura
The price is P18,618
P28,045 total
includes taxes & fees
Oct 4 - Oct 5
The Crest - Serenity Oasis Villa
A modern living room with a leather sofa, a coffee table, and a dining area with a table and chairs.

6. Cozy Relaxing Home in Old Harbour

Cozy Relaxing Home in Old Harbour
2.0 star property
Old Harbour
Cozy Relaxing Home in Old Harbour
A beach with clear water, a sandy shore, and buildings in the background.

7. Fisherman's Point Resort

Fisherman's Point Resort
3.0 star property
Ocho Rios
6.0 out of 10, (616 reviews)
"Perfect location 👌"
United States
Shawnette
The price is P5,498
P7,075 total
includes taxes & fees
Oct 2 - Oct 3
Fisherman's Point Resort
Two beach chairs with colorful covers, a cruise ship in the background, and clear blue water.

8. SandCastles Deluxe Beach Resort

SandCastles Deluxe Beach Resort
3.5 star property
Ocho Rios
7.4 out of 10, Good, (136 reviews)
"I like the room it was clean and spacious Staff professional pool was clean I like everything"
United States
Blossom
SandCastles Deluxe Beach Resort
A living room with a sofa, a coffee table, a TV, and a bookshelf.

9. 1BR Comfort 15 mins Ocho Rios

1BR Comfort 15 mins Ocho Rios
2.0 star property
Richmond Estate
The price is P7,322
P15,055 total
includes taxes & fees
Oct 7 - Oct 8
1BR Comfort 15 mins Ocho Rios
A kitchen with wooden cabinets, a stainless steel sink, a microwave, and a gas stove.

10. Royal Palm Luxury Villas

Royal Palm Luxury Villas
3.0 star property
Ocho Rios
The price is P31,936
P46,176 total
includes taxes & fees
Oct 13 - Oct 14
Royal Palm Luxury Villas
A rectangular swimming pool with a smaller section and a separate hot tub area, surrounded by outdoor seating and potted plants.

11. DraxHall Villa with Private Pool

DraxHall Villa with Private Pool
2.5 star property
Saint Ann's Bay
The price is P22,530
P34,108 total
includes taxes & fees
Oct 2 - Oct 3
DraxHall Villa with Private Pool
A wooden table with two puzzle boxes, surrounded by wooden chairs, in a covered outdoor area with windows.

12. Comfy 3BR Villa - Paradisiac Beach Club

Comfy 3BR Villa - Paradisiac Beach Club
2.0 star property
St. Ann Parish
The price is P23,938
P34,163 total
includes taxes & fees
Oct 2 - Oct 3
Comfy 3BR Villa - Paradisiac Beach Club
A balcony with ornate metal railings and a tiled floor, offering a view of a lush green landscape.

13. Blue Berry Hills Villa

Blue Berry Hills Villa
3.0 star property
Dumbarton
The price is P48,814
P62,457 total
includes taxes & fees
Oct 2 - Oct 3
Blue Berry Hills Villa
A living room with two sofas, a coffee table, and a television.

14. 3BR Family Villa at The Crest

3BR Family Villa at The Crest
2.0 star property
St. Ann Parish
The price is P22,530
P30,665 total
includes taxes & fees
Oct 5 - Oct 6
3BR Family Villa at The Crest
A covered balcony with white balustrades, a stone floor, and a view of greenery.

15. Sandy Bay Paradise Retreat - 7 Bedrooms

Sandy Bay Paradise Retreat - 7 Bedrooms
3.0 star property
Sandy Bay
The price is P27,996
P34,058 total
includes taxes & fees
Oct 13 - Oct 14
Sandy Bay Paradise Retreat - 7 Bedrooms
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middlesex County Hotel Reviews

Bahia Principe Escape Runaway Bay - Hyatt Inclusive Collection - Adults Only - All Inclusive

Bahia Principe Escape Runaway Bay - Hyatt Inclusive Collection - Adults Only - All Inclusive

10/10 Excellent
"Good customer service definitely definitely clean environment welcoming filling. The resort was just full of great people. We were on the adult only side and just had a great time. Very very spacious room large big small TV though lol but other than that really really great time."
Justin 3-night trip
Posted 10 hours ago
Bahia Principe Escape Runaway Bay - Hyatt Inclusive Collection - Adults Only - All Inclusive

Find out more about Middlesex County

Search for holiday rentals in Middlesex County on Expedia! You can easily find your home rentals, villas, holiday apartments in Middlesex County using one of the methods below:

  • View our selection of featured holiday rentals in Middlesex County
  • Use the map to find apartments and other holiday homes in the Middlesex County neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Middlesex County while they last

Look no further and take a look at our great range of rental properties in Middlesex County!